N,N'-bis(2-cyanoethyl)cyclohexane-1,4-diamine | 1142-40-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(2-cyanoethyl)cyclohexane-1,4-diamine
• 英文别名: N,N'-bis(2-cyanoethyl)-cyclohexane-1,4-diamine；3-[[4-(2-cyanoethylamino)cyclohexyl]amino]propanenitrile
• CAS: 1142-40-1
• 化学式: C₁₂H₂₀N₄
• mdl: MFCD27941722
• 分子量: 220.318
• InChiKey: GPMJQBPVTRRHJO-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  439.3±45.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-cyanoethyl)cyclohexane-1,4-diamine 在 镍 氨 、 氢气 作用下， 50.0 ℃ 、400.01 kPa 条件下， 反应 4.0h， 以93.7%的产率得到N,N'-bis(3-aminopropyl)cyclohexane-1,4-diamine
  参考文献：
  名称：

  COMPOUNDS USED TO TREAT ALCOHOLISM

  摘要：

  化合物N,N'-双(3-氨基丙基)环己烷-1,4-二胺，化学式为（I），是一种新的化合物，通过Raney镍催化剂对N,N'-双(2-氰乙基)环己烷-1,4-二胺进行氢化制备而成，后者是由1,4-环己二胺和丙烯腈反应制备而成。将（I）的四甲烷磺酸单水合物口服给遗传性酗酒大鼠（来自智利大学的UChB品系），可显著减少饮酒量。该活性在治疗期后持续一段时间。此外，几乎没有二硫化物样的不良反应，这是与某些抗酒精药物（如氰胺钙或二硫化物本身）的不愉快使用相比的优势。因此，本发明的化合物可用于制备治疗和/或预防哺乳动物，包括人类酗酒症的药物。

  公开号：

  EP1403243A1
• 作为产物：
  描述：

  1,4-环己烷二胺 、 丙烯腈 在 乙醇 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以952.2 g (92.8%) of the title compound were obtained as a brown solid的产率得到N,N'-bis(2-cyanoethyl)cyclohexane-1,4-diamine
  参考文献：
  名称：

  Compounds used to treat alcoholism

  摘要：

  化合物N,N'-双(3-氨丙基)环己烷-1,4-二胺(I)是一种新化合物，通过使用Raney镍催化剂对N,N'-双(2-氰乙基)环己烷-1,4-二胺进行氢化制备，后者是由1,4-环己二胺和丙烯腈反应制备而成。将(I)的四甲烷磺酸盐一水合物口服给遗传性酗酒大鼠（来自智利大学UChB株系），可以显著减少饮酒量。治疗期后，该活性持续一段时间。此外，几乎没有二硫化钴类似的不良反应，这是与一些抗酒精药物如氰胺钙或二硫化钴本身的不愉快使用相比的优势。因此，本发明的化合物可用于制备哺乳动物，包括人类的治疗和/或预防酗酒的药物。

  公开号：

  US07026514B2

文献信息

• COMPOUNDS USED TO TREAT ALCOHOLISM
  申请人：Garbil Pharma Investigacion Chile Ltda.

  公开号：EP1403243A1

  公开（公告）日：2004-03-31

  N,N'-bis(3-aminopropyl)cyclohexane-1,4-diamine, of formula (I), is a new compound that is prepared by hydrogenation with Raney nickel catalyst of N,N'-bis(2-cyanoethyl)-cyclohexane-1,4-diamine, the latter being prepared by reaction between 1,4-cyclohexanediamine and acrylonitrile. The oral administration to genetically alcoholic rats (from the strain UChB of the University of Chile) of the tetrametanesulfonate monohydrate of (I) causes a significant reduction in the alcohol consumption. The activity lasts for some time after the treatment period. Besides, there is a virtually null disulfiram-like adverse effect, what constitutes an advantage over the unpleasant use of some anti-alcoholism agents, such as calcium cyanamide or disulfiram itself. Therefore, the compounds of the invention are useful for the preparation of medicaments for the therapeutic and/or prophylactic treatment of alcoholism in mammals, including human beings.

  化合物N,N'-双(3-氨基丙基)环己烷-1,4-二胺，化学式为（I），是一种新的化合物，通过Raney镍催化剂对N,N'-双(2-氰乙基)环己烷-1,4-二胺进行氢化制备而成，后者是由1,4-环己二胺和丙烯腈反应制备而成。将（I）的四甲烷磺酸单水合物口服给遗传性酗酒大鼠（来自智利大学的UChB品系），可显著减少饮酒量。该活性在治疗期后持续一段时间。此外，几乎没有二硫化物样的不良反应，这是与某些抗酒精药物（如氰胺钙或二硫化物本身）的不愉快使用相比的优势。因此，本发明的化合物可用于制备治疗和/或预防哺乳动物，包括人类酗酒症的药物。
• Compounds used to treat alcoholism
  申请人：——

  公开号：US20040180967A1

  公开（公告）日：2004-09-16

  N,N′-bis(3-aminopropyl)cyclohexane-1,4-diamine, of formula (I), is a new compound that is prepared by hydrogenation with Raney nickel catalyst of N,N′-bis(2-cyanoethyl)-cyclohexane-1,4-diamine, the latter being prepared by reaction between 1,4-cyclohexanediamine and acrylonitrile. The oral administration to genetically alcoholic rats (from the strain UChB of the University of Chile) of the tetrametanesulfonate monohydrate of (I) causes a significant reduction in the alcohol consumption. The activity lasts for some time after the treatment period. Besides, there is a virtually null disulfiram-like adverse effect, what constitutes an advantage over the unpleasant use of some anti-alcoholism agents, such as calcium cyanamide or disulfiram itself. Therefore, the compounds of the invention are useful for the preparation of medicaments for the therapeutic and/or prophylactic treatment of alcoholism in mammals, including human beings. 1

  化学式为（I）的N，N'-双（3-氨丙基）环己烷-1,4-二胺是一种新化合物，通过用Raney镍催化剂对N，N'-双（2-氰乙基）环己烷-1,4-二胺进行加氢制备而成，后者是通过1,4-环己二胺和丙烯腈反应制备的。将（I）的四甲烷磺酸单水合物口服给遗传性酗酒大鼠（来自智利大学UChB的品系），可以显著减少饮酒量。该活性在治疗期后持续一段时间。此外，几乎没有二硫化钴类似的不良反应，这是与一些抗酒精药物（如氰胺钙或二硫化钴本身）的不愉快使用相比的优势。因此，本发明的化合物对于制备哺乳动物，包括人类的酒精中毒的治疗和/或预防药物是有用的。
• US7026514B2
  申请人：——

  公开号：US7026514B2

  公开（公告）日：2006-04-11
• A new polyamine derivative, a structural analog of spermine, with in vivo activity as an inhibitor of ethanol appetite
  作者：María Font、Carmen Sanmartín、Hernán García、Selfa Contreras、Carlos Paeile、Norberto Bilbeny

  DOI：10.1016/j.bmc.2005.04.067

  日期：2005.7

  yThis report describes the design and synthesis of the synthetic polyamine DCD (N,N'-bis-(3-aminopropyl)cyclohexane-1,4-diamine, tetramethanesulfonate), a structural analog of spermine, and its in vivo activity as an inhibitor of alcohol consumption in a free-choice paradigm carried out on genetically high-ethanol-consuming UChB rats. After acute treatment with DCD (daily single dose, 20 mg/kg, p.o., 3 days), a 19% decrease in ethanol intake was obtained, without affecting the levels of food and water intake. After chronic treatment (daily single dose, 20 mg/kg, p.o., 60 days) a decrease of up to 60% in ethanol intake with respect to the basal period was provoked; this effect was significantly maintained during the post-treatment period and, according to the data obtained from the determination of acetaldehyde levels in blood, was not related to a possible disulfiram-like effect. The design of this new compound was carried out using molecular modeling techniques, with the structures of natural polyamines (putrescine, spermidine, and spermine) and biosynthetically related diamines (1,3-diaminopropane; DAP) as templates. These polyamines have shown activity as inhibitors of ethanol appetite in the same experimental model. (c) 2005 Elsevier Ltd. All rights reserved.